This invention relates to herbicidally active sulfonylurea compounds, agriculturally suitable compositions containing such compounds and a method of their use as herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
Even though there are sulfonylurea herbicides which exhibit excellent selectivity on a number of crops while controlling weeds at very low application rates there continues to be a need for herbicides that display such selectivity while controlling weeds.
U.S. Pat. No. 4,514,211 discloses herbicidal sulfonamides of formula ##STR1## wherein L is ##STR2## R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 is H, Cl, CH.sub.3, CF.sub.3, OCH.sub.3, Br, F, SCH.sub.3, or OCF.sub.2 H; PA1 R.sub.5 is H, CH.sub.3, OCH.sub.3, Cl, Br, NO.sub.2, CO.sub.2 R.sub.7, SO.sub.2 R.sub.8, OSO.sub.2 R.sub.9, SO.sub.2 NR.sub.10 R.sub.11, F, CF.sub.3, SCH.sub.3, OCF.sub.2 H or SO.sub.2 N(OCH.sub.3)CH.sub.3 ; and PA1 Q is O, S, SO or SO.sub.2. PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, CH.sub.3, OCH.sub.3, Cl, Br, CO.sub.2 R.sub.5, SO.sub.2 R.sub.6, OSO.sub.2 R.sub.7 or SO.sub.2 NR.sub.8 R.sub.9 ; PA1 R.sub.2 and R.sub.3 are independently H or C.sub.1 -C.sub.3 alkyl; and PA1 R.sub.4 is H or CH.sub.3. PA1 A and A.sup.2 are independently C(O)QR.sup.8, C(T)R.sup.9, Cl, F, Br, NO.sub.2, CH.sub.3, SO.sub.2 NR.sup.1 R.sup.2, SO.sub.2 N(CH.sub.3)(OCH.sub.3), S(O).sub.n R.sup.3, OR.sup.3, OSO.sub.2 R.sup.3 or OSO.sub.2 CF.sub.3 ; PA1 B is SO.sub.2 NHC(W)NR.sup.4 R.sup.5 or SO.sub.2 N.dbd.C(WR.sup.6)NHR.sup.5. PA1 R is H, Cl, Br, NO.sub.2, QR.sub.2, CO.sub.2 R.sub.3, SO.sub.2 NR.sub.5 R.sub.6, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.7 or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.8 is H, CH.sub.3 or Cl; and PA1 R.sub.9 is H or CH.sub.3. PA1 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 and R.sub.4 are independently H, C.sub.1 C.sub.4 alkyl, Cl or Br; and PA1 R.sub.5 is H or CH.sub.3. PA1 R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkythio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy. PA1 R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are H or CH.sub.3 ; or CR.sub.1 R.sub.2 and CR.sub.3 C.sub.4 are C.dbd.O. PA1 A is an unsubstituted or substituted unsaturated bridge of 4 atoms, of the formula --CH.dbd.CH--Y--, wherein Y is a bridge member of 2 atoms which is selected from the series consisting of --NH--CO--, --NH--SO.sub.2 --, --S--CO--, --S--SO.sub.2 --, --O--CO-- or --O--SO.sub.2 --. PA1 Q is O, S, SO or SO.sub.2 ; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H or CH.sub.3 ; PA1 R.sub.2 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, ##STR15## Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 (C.sub.2 -C.sub.4 alkenyl), Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.3 alkoxy), ##STR16## P(O)(CH.sub.3).sub.2, P(O)(OCH.sub.3).sub.2, CN, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.3 -C.sub.4 cycloalkylcarbonyl, NR.sub.9 R.sub.10 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkenyloxy, C.sub.2 -C.sub.3 haloalkenyloxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), NO.sub.2, CN, C.sub.1 -C.sub.2 alkylcarbonyl, OH, NR.sub.9 R.sub.10, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SCN, P(O)(OCH.sub.3).sub.2 or SO.sub.2 NR.sub.11 R.sub.12 ; PA1 R.sub.5 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.6 is H or CH.sub.3 ; PA1 R.sub.7 is H or CH.sub.3 ; PA1 R.sub.8 is H, F, Cl, Br, CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.10 is H or C.sub.1 -C.sub.3 alkyl; or PA1 R.sub.9 and R.sub.10 may be taken together to form (CH.sub.2).sub.4, (CH.sub.2).sub.5 or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 ; PA1 R.sub.11 and R.sub.12 are independently H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.13 is H, C.sub.1 -C.sub.3 alkyl, Cl or Br; PA1 R.sub.14 is H, CH.sub.3, Cl or Br; PA1 A is ##STR17## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, ##STR18## m is 2 or 3; Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and PA1 Z.sub.1 is CH or N; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; and PA1 (b) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (c) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR19## (d) when R.sub.1 is CH.sub.3, then n is O; (e) when J is J-6, then R.sub.1 and R.sub.2 are not both H; PA1 (f) when the total number of carbons of X and Y is greater than four, then the number of carbons of R.sub.4 must be less than or equal to three; PA1 (g) X.sub.4 and Y.sub.4 may not simultaneously be Cl; PA1 (h) when J is J-12, then R.sub.4 is other than C.sub.1 -C.sub.4 alkylcarbonyl; and PA1 (i) when J is J-9, then R.sub.4 is other than CN. PA1 J is J-1, J-2 or J-3; PA1 R.sub.2 is H or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, ##STR20## Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 (C.sub.2 -C.sub.4 alkenyl), Si(CH.sub.3).sub.2 -(C.sub.1 -C.sub.3 alkoxy), ##STR21## P(O)(CH.sub.3).sub.2, P(O)(OCH.sub.3).sub.2, NR.sub.8 R.sub.9 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkenyloxy, C.sub.2 -C.sub.3 haloalkenyloxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), NO.sub.2, CN, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SCN, P(O)(OCH.sub.3).sub.2 or SO.sub.2 NR.sub.10 R.sub.11 ; PA1 A is ##STR22## Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, ##STR23## provided that (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; and PA1 (b) when X or Y is OCH.sub.2 H, then Z is CH. PA1 J is J-1, J-2, J-3, J-4, J-5 or J-6; PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, ##STR24## Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 (C.sub.2 -C.sub.4 alkenyl), Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.3 alkoxy), ##STR25## P(O)(CH.sub.3).sub.2, P(O)(OCH.sub.3).sub.2, CN, NR.sub.9 R.sub.10 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkenyloxy, C.sub.2 -C.sub.3 haloalkenyloxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), NO.sub.2, CN, NR.sub.9 R.sub.10, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SCN, P(O)(OCH.sub.3).sub.2 or SO.sub.2 NR.sub.11 R.sub.12 ; and PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxylalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, C.sub.2 -C.sub.5 alkylsulfinylalkyl, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, ##STR26## under the provisos (a) through (f) except that in proviso (b), Z is CH when X or Y is OCF.sub.2 H. PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, ##STR27## Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 (C.sub.2 -C.sub.4 alkenyl), Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.3 alkoxy), ##STR28## P(O)(CH.sub.3).sub.2, P(O)(OCH.sub.3).sub.2, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.3 -C.sub.4 cycloalkylcarbonyl, NR.sub.9 R.sub.10 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkenyloxy, C.sub.2 -C.sub.3 haloalkenyloxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), NO.sub.2, CN, C.sub.1 -C.sub.2 alkylcarbonyl, OH, NR.sub.9 R.sub.10, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SCN, P(O)(OCH.sub.3).sub.2 or SO.sub.2 NR.sub.11 R.sub.12. PA1 W is O; PA1 R is H; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SCH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, ##STR29## OCF.sub.2 H, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3 ; and Z is CH or N; and PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, cyclopropylmethyl, Si(CH.sub.3).sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 P(O)(OCH.sub.3).sub.2, CHO, C(O)CH.sub.3, CH.sub.2 CHO, CH.sub.2 CO.sub.2 CH.sub.3 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, CN, OH or SO.sub.2 N(CH.sub.3).sub.2. PA1 R.sub.1 is H; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is H; PA1 R.sub.5 is H or CH.sub.3 ; PA1 R.sub.6 is H; PA1 R.sub.7 is H; PA1 R.sub.8 is H; PA1 R.sub.13 is H, CH.sub.3 or Cl; PA1 R.sub.14 is H, CH.sub.3 or Cl; and PA1 Q is O, S or SO.sub.2. PA1 R.sub.4 is ortho to the sulfonylurea bridge and is selected from Si(CH.sub.3).sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 SO.sub.2 CH.sub.3, CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3, CH.sub.2 CN, CH.sub.2 CH.sub.2 CN or CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 ; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl. PA1 J is J-1, J-2, J-3, J-4, J-5 or J-6; and PA1 R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, ##STR30## Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), Si(CH.sub.3).sub.2 (C.sub.2 -C.sub.4 alkenyl), Si(CH.sub.3).sub.2 -(C.sub.1 -C.sub.3 alkoxy), ##STR31## P(O)(CH.sub.3).sub.2, P(O)(OCH.sub.3).sub.2, CN, NR.sub.9 R.sub.10 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.3 alkenyloxy, C.sub.2 -C.sub.3 haloalkenyloxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfinyl, C.sub.1 -C.sub.3 haloalkylsulfonyl, Si(CH.sub.3).sub.2 (C.sub.1 -C.sub.4 alkyl), NO.sub.2, CN, NR.sub.9 R.sub.10, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SCN, P(O)(OCH.sub.3).sub.2 or SO.sub.2 NR.sub.11 R.sub.12. PA1 X' is a reactive halogen.
U.S. Pat. No. 4,492,596 discloses, in part, herbicidal sulfonamides of formula ##STR3## wherein Q is O, S or SO.sub.2 ;
U.S. Pat. No. 4,370,479 discloses herbicidal sulfonamides of formula ##STR4## wherein A.sup.1 is H, F, Cl, Br, CH.sub.3 O or NO.sub.2 ;
U.S. Pat. No. 4,465,506 discloses, in part, herbicidal sulfonamides of formula ##STR5## wherein L is SO.sub.2 NHC(O)NR.sub.10 R.sub.1 ;
U.S. Pat. No. 4,369,320 discloses, in part, herbicidal sulfonamides of formula ##STR6## wherein A is ##STR7## and R.sub.1 is H, F, Cl, Br, OCH.sub.3, CH.sub.3, NO.sub.2, CO.sub.2 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.6.
EP-A-107,979 (published 5/9/84) discloses herbicidal sulfonamides of formula ##STR8## wherein J is, in part, ##STR9## R.sub.1 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, CF.sub.3, SCH.sub.3 or OCF.sub.2 H;
South African patent application 83/5156, published Jan. 16, 1984, discloses herbicidal sulfonylureas of the general structure shown below: ##STR10## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group; and
EP-A-123,303 (published 10/31/84) discloses herbicidal sulfonamides of formula ##STR11## wherein R is H, halogen, CH.sub.3, NO.sub.2, alkoxycarbonyl, alkysulphonyl, aminocarbonyl, mono- or dialkylaminocarbonyl, alkoxy (optionally substituted by 1-3 halogen), alkynyloxy, aryloxy or NR.sub.7 COR.sub.8 ;
South African patent application 84/3522 (published 11/11/84) discloses herbicidal sulfonamides of formula ##STR12## wherein R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, CN, XR.sup.5, COXR.sup.6, CONR.sup.7 R.sup.8, SOR.sup.9 or SO.sub.2 R.sup.10 ;
A part of this disclosure is carried by U.S. Pat. No. 4,589,911, issued May 20, 1986.